Sodium Carbonate → 5-(4-Chlorobutyl)-1-methyl-1H-pyrazole-3-carbonitrile

HRID 1984428Notes

Reaction equation

HRID 1984428 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([C:12]([NH2:14])=O)[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([C:12]#[N:14])[CH:7]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 66958721HCID 66958721, compound

Product 1

HCID 669586685-(4-Chlorobutyl)-1-methyl-1H-pyrazole-3-carbonitrile

Conditions

Temperature
90 °C

Procedure

A modification of the method described in Part E of Examples 1-4 was used to treat 5-(4-hydroxybutyl)-1-methyl-1H-pyrazole-3-carboxamide (42.9 g, 218 mmol) with phosphorous oxychloride (130 mL). The reaction was heated for two hours at 90° C. before cooling to 0° C. and pouring into ice water. The mixture was adjusted to pH 12 with the addition of 2 N aqueous sodium carbonate and 50% aqueous sodium hydroxide. The mixture was extracted with chloroform. The combined extracts were passed through a layer of silica gel (eluting first with chloroform and then with ethyl acetate to provide 23.0 g of 5-(4-chlorobutyl)-1-methyl-1H-pyrazole-3-carbonitrile as a dark oil that was used in the next step without further purification.

Workup

  1. temperaturebefore cooling to 0° C.
  2. extractionThe mixture was extracted with chloroform
  3. washeluting first with chloroform

Sources & evidence

ORD record
ord-ffc43e00f17b4e80962e5b45d8795919
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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